EP3652224A1 - Process for the production of isobutene polymers with improved temperature control - Google Patents
Process for the production of isobutene polymers with improved temperature controlInfo
- Publication number
- EP3652224A1 EP3652224A1 EP18738295.7A EP18738295A EP3652224A1 EP 3652224 A1 EP3652224 A1 EP 3652224A1 EP 18738295 A EP18738295 A EP 18738295A EP 3652224 A1 EP3652224 A1 EP 3652224A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- aluminum
- process according
- butene
- reaction medium
- chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 33
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 74
- 239000000178 monomer Substances 0.000 claims abstract description 72
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 36
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 35
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000003085 diluting agent Substances 0.000 claims description 58
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 57
- -1 hydrocarbon radical Chemical class 0.000 claims description 55
- 239000003999 initiator Substances 0.000 claims description 51
- 150000003254 radicals Chemical group 0.000 claims description 43
- 239000012429 reaction media Substances 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 9
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims description 9
- 229910052782 aluminium Chemical group 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 150000003460 sulfonic acids Chemical class 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 5
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 claims description 3
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 claims description 3
- JFICPAADTOQAMU-UHFFFAOYSA-L ethylaluminum(2+);dibromide Chemical compound CC[Al](Br)Br JFICPAADTOQAMU-UHFFFAOYSA-L 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- DKRDVQXZJNVXDP-UHFFFAOYSA-M bromo(dibutyl)alumane Chemical compound [Br-].CCCC[Al+]CCCC DKRDVQXZJNVXDP-UHFFFAOYSA-M 0.000 claims description 2
- NZIXICKPQWIFAU-UHFFFAOYSA-K bromo(dimethyl)alumane;dibromo(methyl)alumane Chemical compound C[Al](C)Br.C[Al](Br)Br NZIXICKPQWIFAU-UHFFFAOYSA-K 0.000 claims description 2
- QQHRHLXGCZWTDK-UHFFFAOYSA-L butylaluminum(2+);dibromide Chemical compound [Br-].[Br-].CCCC[Al+2] QQHRHLXGCZWTDK-UHFFFAOYSA-L 0.000 claims description 2
- SHOVVTSKTTYFGP-UHFFFAOYSA-L butylaluminum(2+);dichloride Chemical compound CCCC[Al](Cl)Cl SHOVVTSKTTYFGP-UHFFFAOYSA-L 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- HYZXMVILOKSUKA-UHFFFAOYSA-K chloro(dimethyl)alumane;dichloro(methyl)alumane Chemical compound C[Al](C)Cl.C[Al](Cl)Cl HYZXMVILOKSUKA-UHFFFAOYSA-K 0.000 claims description 2
- VJRUISVXILMZSL-UHFFFAOYSA-M dibutylalumanylium;chloride Chemical compound CCCC[Al](Cl)CCCC VJRUISVXILMZSL-UHFFFAOYSA-M 0.000 claims description 2
- ZGMHEOLLTWPGQX-UHFFFAOYSA-M dimethylalumanylium;bromide Chemical compound C[Al](C)Br ZGMHEOLLTWPGQX-UHFFFAOYSA-M 0.000 claims description 2
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- XBKBZMOLSULOEA-UHFFFAOYSA-L methylaluminum(2+);dibromide Chemical compound C[Al](Br)Br XBKBZMOLSULOEA-UHFFFAOYSA-L 0.000 claims description 2
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 4
- 229910052796 boron Inorganic materials 0.000 claims 4
- 150000001399 aluminium compounds Chemical class 0.000 claims 2
- 229940077746 antacid containing aluminium compound Drugs 0.000 claims 2
- NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 claims 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 59
- 239000007788 liquid Substances 0.000 abstract description 12
- 229920002367 Polyisobutene Polymers 0.000 abstract description 9
- 229920005549 butyl rubber Polymers 0.000 abstract description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
- 239000002841 Lewis acid Substances 0.000 description 38
- 150000007517 lewis acids Chemical class 0.000 description 38
- 239000000203 mixture Substances 0.000 description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 22
- 229910052801 chlorine Inorganic materials 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 17
- 125000003710 aryl alkyl group Chemical group 0.000 description 16
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 16
- 150000002367 halogens Chemical group 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002002 slurry Substances 0.000 description 14
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 12
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 12
- 150000001540 azides Chemical class 0.000 description 12
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 12
- 239000012948 isocyanate Substances 0.000 description 12
- 150000002513 isocyanates Chemical class 0.000 description 12
- 150000002540 isothiocyanates Chemical class 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 229940050176 methyl chloride Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 7
- 239000003507 refrigerant Substances 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 6
- 239000002808 molecular sieve Substances 0.000 description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- XAZKFISIRYLAEE-UHFFFAOYSA-N (+-)-trans-1,3-Dimethyl-cyclopentan Natural products CC1CCC(C)C1 XAZKFISIRYLAEE-UHFFFAOYSA-N 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 3
- WGECXQBGLLYSFP-UHFFFAOYSA-N 2,3-dimethylpentane Chemical compound CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,3-dimethylpentane Natural products CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical class CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 3
- RIRARCHMRDHZAR-UHFFFAOYSA-N (+-)-trans-1,2-Dimethyl-cyclopentan Natural products CC1CCCC1C RIRARCHMRDHZAR-UHFFFAOYSA-N 0.000 description 2
- INPRTAFPJCUIBZ-OWOJBTEDSA-N (e)-1,3-difluoroprop-1-ene Chemical compound FC\C=C\F INPRTAFPJCUIBZ-OWOJBTEDSA-N 0.000 description 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 2
- 229940051271 1,1-difluoroethane Drugs 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- MJMQIMYDFATMEH-UHFFFAOYSA-N 2-chloro-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)Cl MJMQIMYDFATMEH-UHFFFAOYSA-N 0.000 description 2
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 description 2
- MRFQFQYRTNGOCZ-UHFFFAOYSA-N 2-methoxypropan-2-ylbenzene Chemical compound COC(C)(C)C1=CC=CC=C1 MRFQFQYRTNGOCZ-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- XPMMKIYJJWQFOR-UHFFFAOYSA-N 2-phenylpropan-2-yl acetate Chemical compound CC(=O)OC(C)(C)C1=CC=CC=C1 XPMMKIYJJWQFOR-UHFFFAOYSA-N 0.000 description 2
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 2
- SFRKSDZMZHIISH-UHFFFAOYSA-N 3-ethylhexane Chemical compound CCCC(CC)CC SFRKSDZMZHIISH-UHFFFAOYSA-N 0.000 description 2
- AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical compound CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 2
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
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- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- GQIJYUMTOUBHSH-IJIVKGSJSA-N piperyline Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCC1 GQIJYUMTOUBHSH-IJIVKGSJSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LTEDQKPGOZDGRZ-UHFFFAOYSA-L propan-2-olate;titanium(4+);dichloride Chemical compound Cl[Ti+2]Cl.CC(C)[O-].CC(C)[O-] LTEDQKPGOZDGRZ-UHFFFAOYSA-L 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- 150000005377 tertiary alkyl halides Chemical class 0.000 description 1
- ZLUPPMYQLOZJPZ-UHFFFAOYSA-N tetrachloro(fluoro)-$l^{5}-arsane Chemical compound F[As](Cl)(Cl)(Cl)Cl ZLUPPMYQLOZJPZ-UHFFFAOYSA-N 0.000 description 1
- IOKNOYHQNVGVTM-UHFFFAOYSA-J tetrachloro(methoxy)-$l^{5}-stibane Chemical compound CO[Sb](Cl)(Cl)(Cl)Cl IOKNOYHQNVGVTM-UHFFFAOYSA-J 0.000 description 1
- HBBBDGWCSBWWKP-UHFFFAOYSA-J tetrachloroantimony Chemical compound Cl[Sb](Cl)(Cl)Cl HBBBDGWCSBWWKP-UHFFFAOYSA-J 0.000 description 1
- CHPGDDYKLVMZGY-UHFFFAOYSA-M tetraphenylstibanium;chloride Chemical compound C=1C=CC=CC=1[Sb](C=1C=CC=CC=1)(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 CHPGDDYKLVMZGY-UHFFFAOYSA-M 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- UTCMPRJXBKPRFM-UHFFFAOYSA-J titanium(4+) acetate trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Ti+4].CC([O-])=O UTCMPRJXBKPRFM-UHFFFAOYSA-J 0.000 description 1
- SVCIFVXZFRRVIV-UHFFFAOYSA-K trichloro(dimethoxy)-$l^{5}-stibane Chemical compound CO[Sb](Cl)(Cl)(Cl)OC SVCIFVXZFRRVIV-UHFFFAOYSA-K 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 description 1
- ZCPSWAFANXCCOT-UHFFFAOYSA-N trichloromethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)S(Cl)(=O)=O ZCPSWAFANXCCOT-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JNLSTWIBJFIVHZ-UHFFFAOYSA-K trifluoroindigane Chemical compound F[In](F)F JNLSTWIBJFIVHZ-UHFFFAOYSA-K 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical group Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- KJXQRYHLQNYJJE-UHFFFAOYSA-J vanadium(4+) bromide trichloride Chemical compound [Cl-].[Cl-].[Cl-].[V+4].[Br-] KJXQRYHLQNYJJE-UHFFFAOYSA-J 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
- 238000000196 viscometry Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
- C08F210/12—Isobutene with conjugated diolefins, e.g. butyl rubber
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/08—Isoprene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
- C08F4/14—Boron halides or aluminium halides; Complexes thereof with organic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2400/00—Characteristics for processes of polymerization
- C08F2400/02—Control or adjustment of polymerization parameters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/005—Friedel-Crafts catalysts in general
Definitions
- the invention relates to an efficient process for the preparation of isoolefin polymers such as polyisobutene or butyl rubber by polymerization of a liquid medium comprising the monomer(s) and ethane or carbon dioxide that is substantially dissolved therein.
- Polymers containing repeating units derived from isoolefins are industrially prepared by carbocationic polymerization processes. Of particular importance are polyisobutene and butyl rubber which is a copolymer of isobutylene and a smaller amount of a multiolefin such as isoprene.
- the carbocationic polymerization of isoolefins and its copolymerization with multiolefins is mechanistically complex.
- the catalyst system is typically composed of two components: an initiator and a Lewis acid such as aluminum trichloride which is frequently employed in large scale commercial processes.
- initiators include proton sources such as hydrogen halides, alcohols, phenols, carboxylic and sulfonic acids and water.
- the isoolefin reacts with the Lewis acid and the initiator to produce a carbenium ion which further reacts with a monomer forming a new carbenium ion in the so- called propagation step.
- the type of monomers, the type of diluent or solvent and its polarity, the polymerization temperature as well as the specific combination of Lewis acid and initiator affects the chemistry of propagation and thus monomer incorporation into the growing polymer chain.
- the slurry polymerization process in methyl chloride offers the advantage that a polymer concentration of up to 40 wt- % and more in the reaction mixture can be achieved, as opposed to a polymer concentration of typically at technically feasible maximum 20 wt.-% in solution polymerizations depending on the targeted molecular weight.
- An acceptable relatively low viscosity of the polymerization solution has to be maintained enabling the heat of polymerization to be removed via heat exchange across the surface of the reaction device .
- Slurry and solution polymerization processes in methyl chloride or alkanes are used in the production of high molecular weight polyisobutylene and isobutylene-isoprene butyl rubber polymers.
- aliphatic solvents like normal and iso pentanes and hexanes as well as mixtures are used for polymerization as for examples disclosed in WO2010/006983 A and WO201 1/089092A which have significant advantages in the downstream processing e.g. chemical modification of the polymer.
- the butyl rubber prepared during polymerization is dissolved in these aliphatic media and so these processes are normally referred to as a solution processes.
- a common feature of both, slurry and solution processes is that due to the high reactivity of the initiators employed temperature control and the avoidance of so called "hot spots" due to inhomogenities of the polymerization medium is difficult but crucial to achieve a desired product quality and to avoid reactor fouling, i.e. the formation of deposits of polymers on the surfaces of the reactor. Such deposits, due to their insulating effect, reduce cooling efficiency and may cause a rapid rise of temperature within the reactor thereby increasing the rate of the exothermic polymerization and fast production of further heat which is again insufficiently removed. Finally, this may even lead to a thermal runaway.
- GB 543,308 discloses the use of solid carbon dioxide as refrigerant in the batch copolymerization of isobutene and butadiene at -78°C.
- reaction medium comprising an organic diluent and at least one monomer being an isoolefin and ethane or carbon dioxide that is substantially dissolved in the reaction medium, and;
- the invention also encompasses all combinations preferred embodiments, ranges parameters as disclosed hereinafter with either each other or with the broadest disclosed range or parameter.
- step a) a reaction medium comprising an organic diluent and at least one monomer being an isoolefin and ethane or carbon dioxide that is substantially dissolved in the reaction medium is provided.
- isoolefin denotes compounds comprising one carbon-carbon-double- bond, wherein one carbon-atom of the double-bond is substituted by two alkyl-groups and the other carbon atom is substituted by two hydrogen atoms or by one hydrogen atom and one alkyl-group.
- suitable isoolefins include isoolefins having from 4 to 16 carbon atoms, preferably 4 to 7 carbon atoms, such as isobutene, 2-methyl- l-butene, 3-methyl-l-butene, 2-methyl-2- butene.
- a preferred isolefin is isobutene.
- the reaction medium may comprise further monomers that are copolymerized with the at least one isoolefin.
- Such further monomers include multiolefins.
- multiolefm denotes compounds comprising more than one carbon- carbon-double-bond, either conjugated or non-conjugated.
- Suitable multiolefins include isoprene, butadiene, 2-methylbutadiene, 2,4- dimethylbutadiene, piperyline, 3-methyl-l,3-pentadiene, 2,4-hexadiene, 2-neopentylbutadiene, 2-methyl- l,5-hexadiene, 2,5-dimethyl-2,4-hexadiene, 2 -methyl- 1 ,4-pentadiene, 4-butyl-l,3- pentadiene, 2,3-dimethyl-l,3-pentadiene, 2,3-dibutyl- l,3-pentadiene, 2-ethyl-l,3-pentadiene, 2- ethyl- 1,3 -butadiene, 2 -methyl- 1 ,6-heptadiene, cyclopentadiene, methylcyclopentadiene, cyclohexadiene and 1-vinyl-cyclo
- Preferred multiolefins are isoprene and butadiene. Isoprene is particularly preferred.
- the reaction medium may comprise further monomers that are copolymerized with the at least one isoolefin and are neither isoolefins nor multiolefins.
- Such further monomers include ⁇ - pinene, styrene, divinylbenzene, diisopropenylbenzene o-, m- and p-alkylstyrenes such as o-, m- and p-methyl-styrene.
- isobutene is used as sole monomer, where sole denotes a fraction of 99.9 wt.-% or more of all monomers employed.
- the monomers employed in step a) may comprise in the range of from 80 wt.-% to 99.5 wt.-%, preferably of from 85 wt.-% to 98.0 wt.-%, more preferably of from 85 wt.-% to 96.5 wt.-%, even more preferably of from 85 wt.-% to 95.0 wt.-%, by weight of at least one isoolefin and in the range of from 0.5 wt.-% to 20 wt.-%, preferably of from 2.0 wt.-% to 15 wt.-%, more preferably of from 3.5 wt.-% to 15 wt.-%, and yet even more preferably of from 5.0 wt.-% to 15 wt.-% by weight of at least one multiolefm based on the weight sum of all monomers employed.
- the monomer mixture comprises in the range of from 90 wt.-% to 95 wt.-% of at least one isoolefin and in the range of from 5 wt.-% to 10 wt.-% by weight of a multiolefm based on the weight sum of all monomers employed.
- the monomer mixture comprises in the range of from 92 wt.-% to 94 wt.-% of at least one isoolefin and in the range of from 6 wt.-% to 8 wt.-% by weight of at least one multiolefm monomer based on the weight sum of all monomers employed.
- the isoolefm is preferably isobutene and the multiolefin is preferably isoprene.
- the multiolefin content of the final copolymers produced are typically 0.1 mol-% or more, preferably of from 0.1 mol-% to 15 mol-%, in another embodiment 0.5 mol-% or more, preferably of from 0.5 mol-% to 10 mol- %, in another embodiment 0.7 mol-% or more, preferably of from 0.7 to 8.5 mol-% in particular of from 0.8 to 1.5 or from 1.5 to 2.5 mol-% or of from 2.5 to 4.5 mol-% or from 4.5 to 8.5 mol- %, particularly where isobutene and isoprene are employed.
- the multiolefin content of copolymers produced according to the invention is 0.1 mol-% or more, preferably of from 0.1 mol-% to 3 mol-%, particularly where isobutene and isoprene are employed.
- the monomers are purified before use in step a), in particular when they are recycled from optional step c).
- Purification of monomers may be carried out by passing through adsorbent columns containing suitable molecular sieves or alumina based adsorbent materials.
- the total concentration of water and substances such as alcohols and other organic oxygenates that act as poisons to the reaction are preferably reduced to less than around 10 parts per million on a weight basis.
- organic diluent encompasses diluting or dissolving organic chemicals which are liquid under reactions conditions. Any suitable organic diluent may be used which does not r not to any appreciable extent react with monomers or components of the initiator system.
- organic diluent includes mixtures of at least two diluents.
- organic diluents examples include hydrochlorocarbon(s) such as methyl chloride, methylene chloride or ethyl chloride.
- organic diluents include hydrofluorocarbons represented by the formula: C x H y F z wherein x is an integer from 1 to 40, alternatively from 1 to 30, alternatively from 1 to 20, alternatively from 1 to 10, alternatively from 1 to 6, alternatively from 2 to 20 alternatively from 3 to 10, alternatively from 3 to 6, most preferably from 1 to 3, wherein y and z are integers and at least one.
- the hydrofluorocarbon(s) is/are selected from the group consisting of saturated hydrofluorocarbons such as fluoromethane; difluoromethane; trifluoromethane; fluoroethane; 1, 1-difluoroethane; 1 ,2-difluoroethane; 1,1, 1-trifluoroethane; 1 , 1 -,2- trifluoroethane; 1 , 1 ,2,2-tetrafluoroethane; 1 , 1 , 1 ,2,2-pentafluoroethane; 1-fluoropropane; 2- fluoropropane; 1, 1-difluoropropane; 1 ,2-difluoropropane; 1,3-difluoropropane; 2,2- difluoropropane; 1 , 1 , 1 -trifluoropropane; 1 , 1 ,2-trifluoropropane; 1, 1,3-trifluoropropane; 1,
- HFC's include difluoromethane, trifluoromethane, 1 , 1 -difluoroethane, 1,1, 1- trifluoroethane, fluoromethane, and 1,1, 1 ,2-tetrafluoroethane.
- the hydro fluorocarbon(s) is/are selected from the group consisting of unsaturated hydrofluorocarbons such as vinyl fluoride; 1,2-difluoroethene; 1,1,2- trifluoroethene; 1 -fluoropropene, 1,1-difluoropropene; 1 ,2-difluoropropene; 1,3- difluoropropene; 2,3-difluoropropene; 3,3-difluoropropene; 1,1,2-trifluoropropene; 1,1,3- trifluoropropene; 1,2,3-trifluoropropene; 1,3,3-trifluoropropene; 2,3,3-trifluoropropene; 3,3,3- trifluoropropene; 2,3,3,3-tetrafluoro-l-propene; 1 -fluoro- 1 -butene; 2-fluoro- 1 -butene; 3-fluoro- 1
- organic diluents include hydrochlorofluorocarbons.
- organic diluents include hydrocarbons, preferably alkanes which in a further preferred embodiment are those selected from the group consisting of n-butane, isobutane, n-pentane, methycyclopentane, isohexane, 2-methylpentane, 3-methylpentane, 2- methylbutane, 2,2-dimethylbutane, 2,3-dimethylbutane, 2-methylhexane, 3-methylhexane, 3- ethylpentane, 2,2-dimethylpentane, 2,3-dimethylpentane, 2,4-dimethylpentane, 3,3-dimethyl pentane, 2-methylheptane, 3-ethylhexane, 2,5-dimethylhexane, 2,2,4,-trimethylpentane, octane, heptane, butane, nonane, decane, dodecane, undecane,
- hydrocarbon diluents include benzene, toluene, xylene, ortho-xylene, para- xylene and meta- xylene.
- Suitable organic diluents further include mixtures of at least two compounds selected from the groups of hydrochlorocarbons, hydrofluorocarbons, hydrochlorofluorocarbons and hydrocarbons. Specific combinations include mixtures of hydrochlorocarbons and hydrofluorocarbons such as mixtures of methyl chloride and 1 , 1 , 1 ,2-tetrafluoroethane, in particular those of 40 to 60 vol.-% methyl chloride and 40 to 60 vol.-% 1, 1,1,2- tetrafluoroethane whereby the aforementioned two diluents add up to 90 to 100 vol.-%, preferably to 95 to 100 vol.% of the total diluent, whereby the potential remainder to 100 vol.% includes other halogenated hydrocarbons; or mixtures of methyl chloride and at least one alkane or mixtures of alkanes such as mixtures comprising at least 90 wt.-%, preferably 95 wt.-% of alkanes having
- At a pressure of 1013 hPa of 100°C or less preferably in the range of from 35 to 100°C, more preferably 90°C or less, even more preferably in the range of from 35 to 90°C.
- the organic diluent is selected to allow a slurry polymerization or a solution polymerization.
- the reaction medium further comprises ethane or carbon dioxide that is substantially dissolved in the reaction medium.
- substantially dissolved means that means that more than 50 wt.-%, preferably at least 70 wt.-%, preferably at least 80 wt.-%, more preferably at least 90 wt.-% and even more preferably at least 95 wt.-% of the ethane or carbon dioxide present in the reaction medium is dissolved therein.
- the remainder may be solid carbon dioxide e.g. suspended in the reaction medium.
- the reaction medium contains no solid carbon dioxide and tis homogenous.
- step b additional ethane or carbon dioxide may be added during step b).
- This addition may be effect for example by injecting liquid ethane or carbon dioxide or adding a solution of carbon dioxide in an organic diluent as described above.
- the monomer(s) may be present in the reaction medium in an amount of from 0.01 wt.-% to 80 wt.-%, preferably of from 0.1 wt-% to 65 wt.-%, more preferably of from 10.0 wt-% to 65.0 wt.-% and even more preferably of from 25.0 wt.-% to 65.0 wt.-%, or in another embodiment of from 10.0 wt.-% to 40.0 wt.-%.
- the organic diluent may be present in the reaction medium in an amount of from 0.01 wt.-% to 80 wt.-%, preferably of from 0.1 wt-% to 65 wt.-%, more preferably of from 10.0 wt.-% to 65.0 wt.-% and even more preferably of from 25.0 wt.-% to 65.0 wt.-%, or in another embodiment of from 10.0 wt.-% to 40.0 wt.-%.
- Ethane or Carbon dioxide may be present in the reaction medium in an amount of from 0.01 wt.-% to 20 wt.-%, preferably of from 0.01 wt.-% to 12 wt.-%, more preferably of from 1,0 wt- % to 12.0 wt.-% and even more preferably of from 5.0 wt.-% to 1 1.0 wt.-%, or in another embodiment of from 5.5 wt.-% to 12.0 wt.-%.
- the amounts of organic diluent, the monomers and the ethane or the carbon dioxide are selected such that they make up at least 95 wt.-%, preferably 97 to 100 wt.-% and more preferably 99 to 100 wt.% of the reaction medium employed in step b).
- the remainder to 100 % may comprise other organic or inorganic compounds, preferably those virtually not affecting the polymerization reaction.
- the reaction medium comprises of from 10.0 wt.-% to 65.0 wt.-% of monomer(s), of from 20.0 wt.-% to 89.9 wt.-% of organic diluent and of from 0.1 wt.-% to 15.0 wt.-% of carbon dioxide whereby the amounts of organic diluent, the monomer(s) and carbon dioxide are selected such that they make up at least 95 wt.-%, preferably 97 to 100 wt.-% and more preferably 99 to 100 wt.% of the reaction medium
- the reaction medium comprises of from 10.0 wt.-% to 65.0 wt.-% of monomer(s), of from 20.0 wt.-% to 89.9 wt.-% of organic diluent and of from 0.1 wt.-% to 15.0 wt.-% of ethane or carbon dioxide whereby the amounts of organic diluent, the monomer(s) and ethane or carbon dioxide are selected such that they make up at least 95 wt.-%, preferably 97 to 100 wt.-% and more preferably 99 to 100 wt.% of the reaction medium
- the reaction medium may be prepared for example by mixing the organic diluent and the monomer(s) and then conveying the resulting mixture over a bed of solid carbon dioxide to allow dissolution of the carbon dioxide into the reaction medium to the desired level. It is typically advantageous to pre-cool the monomer(s), the organic diluent or the mixture thereof to avoid to much consumption of carbon dioxide for cooling down the whole reaction medium.
- a suitable temperature for pre-cooling is typically in the range of from 0 to - 100°, preferably in the range of from -20 to -80°C , more preferably of from -50°C to -80°C.
- step b) the monomer(s) within the reaction medium are polymerized in the presence of an initiator system to form a product medium comprising the polymer, the organic diluent and optionally residual monomers.
- the initiator system comprises at least one Lewis acid and an initiator.
- Suitable Lewis acids include compounds represented by formula MX 3 , where M is a group 13 element and X is a halogen.
- Examples for such compounds include aluminum trichloride, aluminum tribromide, boron trichloride, boron tribromide, gallium trichloride and indium trifluoride, whereby aluminum trichloride is preferred.
- Lewis acids include compounds represented by formula MR (m) X(3_ m ), where M is a group 13 element, X is a halogen, R is a monovalent hydrocarbon radical selected from the group consisting of C1-C12 alkyl, C6-C10 aryl, C7-C14 arylalkyl and C7-C14 alkylaryl radicals; and and m is one or two.
- X may also be an azide, an isocyanate, a thiocyanate, an isothiocyanate or a cyanide.
- Examples for such compounds include methyl aluminum dibromide, methyl aluminum dichloride, ethyl aluminum dibromide, ethyl aluminum dichloride, butyl aluminum dibromide, butyl aluminum dichloride, dimethyl aluminum bromide, dimethyl aluminum chloride, diethyl aluminum bromide, diethyl aluminum chloride, dibutyl aluminum bromide, dibutyl aluminum chloride, methyl aluminum sesquibromide, methyl aluminum sesquichloride, ethyl aluminum sesquibromide, ethyl aluminum sesquichloride and any mixture thereof.
- diethyl aluminum chloride Et 2 AlCl or DEAC
- ethyl aluminum sesquichloride Eti .5 AlCli .5 or EASC
- ethyl aluminum dichloride EtAlC . or EADC
- diethyl aluminum bromide Et 2 AlBr or DEAB
- ethyl aluminum sesquibromide Eti .5 AlBri .5 or EASB
- EtAlBr 2 or EADB diethyl aluminum dibromide
- Lewis acids include compounds represented by formula M(RO) n R m X(3-( m +n)); wherein M is a Group 13 metal; wherein RO is a monovalent hydrocarboxy radical selected from the group consisting of C1-C30 alkoxy, C7-C30 aryloxy, C7-C30 arylalkoxy, C7-C30 alkylaryloxy; R is a monovalent hydrocarbon radical selected from the group consisting of Cr C12 alkyl, C6-C10 aryl, C7-C14 arylalkyl and C7-C14 alkylaryl radicals as defined above; n is a number from 0 to 3 and m is an number from 0 to 3 such that the sum of n and m is not more than 3;
- X is a halogen independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, preferably chlorine.
- X may also be an azide, an isocyanate, a thiocyanate, an isothiocyanate or a cyanide.
- alkoxy and aryloxy are structural equivalents to alkoxides and phenoxides respectively.
- arylalkoxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an alkoxy position.
- alkylaryl refers to a radical containing both aliphatic and aromatic structures, the radical being at an aryloxy position.
- Non-limiting examples of these Lewis acids include methoxyaluminum dichloride, ethoxyaluminum dichloride, 2,6-di-tert-butylphenoxyaluminum dichloride, methoxy methylaluminum chloride, 2,6-di-tert-butylphenoxy methylaluminum chloride, isopropoxygallium dichloride and phenoxy methylindium fluoride.
- Lewis acids include compounds represented by formula
- R' is a monovalent hydrocarbon radical selected from the group consisting of C1-C12 alkyl, C6-C10 aryl, C7-C14 arylalkyl and C7-C14 alkylaryl radicals as defined above
- n is a number from 0 to 3 and m is a number from 0 to 3 such that the sum of n and m is not more than 3
- X is a halogen independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, preferably chlorine.
- X may also be an azide, an isocyanate, a thiocyan
- arylalkylacyloxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an alkyacyloxy position.
- alkylarylacyloxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an arylacyloxy position.
- Lewis acids include acetoxyaluminum dichloride, benzoyloxyaluminum dibromide, benzoyloxygallium difluoride, methyl acetoxyaluminum chloride, and isopropoyloxyindium trichloride.
- Lewis acids include compounds based on metals of Group 4, 5, 14 and 15 of the Periodic Table of the Elements, including titanium, zirconium, tin, vanadium, arsenic, antimony, and bismuth.
- the Group 4, 5 and 14 Lewis acids have the general formula MX 4 ; wherein M is Group 4, 5, or 14 metal; and X is a halogen independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, preferably chlorine. X may also be a azide, an isocyanate, a thiocyanate, an isothiocyanate or a cyanide.
- Non-limiting examples include titanium tetrachloride, titanium tetrabromide, vanadium tetrachloride, tin tetrachloride and zirconium tetrachloride.
- the Group 4, 5, or 14 Lewis acids may also contain more than one type of halogen.
- Non-limiting examples include titanium bromide trichloride, titanium dibromide dichloride, vanadium bromide trichloride, and tin chloride trifluoride.
- Group 4, 5 and 14 Lewis acids useful in this invention may also have the general formula MR n X(4_ n ) ; wherein M is Group 4, 5, or 14 metal; wherein R is a monovalent hydrocarbon radical selected from the group consisting of C1-C12 alkyl, C6-C10 aryl, C7-C14 arylalkyl and C 7 - Ci4 alkylaryl radicals; n is an integer from 0 to 4; X is a halogen independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, preferably chlorine. X may also be an azide, an isocyanate, a thiocyanate, an isothiocyanate or a cyanide.
- arylalkyl refers to a radical containing both aliphatic and aromatic structures, the radical being at an alkyl position.
- alkylaryl refers to a radical containing both aliphatic and aromatic structures, the radical being at an aryl position.
- Non-limiting examples of these Lewis acids include benzyltitanium trichloride, dibenzyltitanium dichloride, benzylzirconium trichloride, dibenzylzirconium dibromide, methyltitanium trichloride, dimethyltitanium difluoride, dimethyltin dichloride and phenylvanadium trichloride.
- Group 4, 5 and 14 Lewis acids useful in this invention may also have the general formula M(RO) n R' m X4 (m+n); wherein M is Group 4, 5, or 14 metal, wherein RO is a monovalent hydrocarboxy radical selected from the group consisting of C1-C30 alkoxy, C7-C30 aryloxy, C 7 - C30 arylalkoxy, C7-C30 alkylaryloxy radicals; R is a monovalent hydrocarbon radical selected from the group consisting of , R is a monovalent hydrocarbon radical selected from the group consisting of C1-C12 alkyl, C6-C10 aryl, C7-C14 arylalkyl and C7-C14 alkylaryl radicals as defined above; n is an integer from 0 to 4 and m is an integer from 0 to 4 such that the sum of n and m is not more than 4; X is selected from the group consisting of fluorine, chlorine, bromine, and iodine,
- alkoxy and aryloxy are structural equivalents to alkoxides and phenoxides respectively.
- arylalkoxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an alkoxy position.
- alkylaryl refers to a radical containing both aliphatic and aromatic structures, the radical being at an aryloxy position.
- Lewis acids include methoxytitanium trichloride, n-butoxytitanium trichloride, di(isopropoxy)titanium dichloride, phenoxytitanium tribromide, phenylmethoxyzirconium trifluoride, methyl methoxytitanium dichloride, methyl methoxytin dichloride and benzyl isopropoxyvanadium dichloride.
- arylalkylacyloxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an alkylacyloxy position.
- alkylarylacyloxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an arylacyloxy position.
- Lewis acids include acetoxytitanium trichloride, benzoylzirconium tribromide, benzoyloxytitanium trifluoride, isopropoyloxytin trichloride, methyl acetoxytitanium dichloride and benzyl benzoyloxyvanadium chloride.
- Group 5 Lewis acids useful in this invention may also have the general formula MOX 3 ; wherein M is a Group 5 metal and wherein X is a halogen independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, preferably chlorine.
- a non-limiting example is vanadium oxytrichloride.
- the Group 15 Lewis acids have the general formula MX y , wherein M is a Group 15 metal and X is a halogen independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, preferably chlorine and y is 3, 4 or 5.
- X may also be an azide, an isocyanate, a thiocyanate, an isothiocyanate or a cyanide.
- Non-limiting examples include antimony hexachloride, antimony hexafluoride, and arsenic pentafluoride.
- the Group 15 Lewis acids may also contain more than one type of halogen.
- Non- limiting examples include antimony chloride pentafluoride, arsenic trifluoride, bismuth trichloride and arsenic fluoride tetrachloride.
- Group 15 Lewis acids useful in this invention may also have the general formula MR n X y _ n; wherein M is a Group 15 metal; wherein R is a monovalent hydrocarbon radical selected from the group consisting of C1-C12 alkyl, C6-C10 aryl, C7-C14 arylalkyl and C7-C14 alkylaryl radicals; and n is an integer from 0 to 4; y is 3, 4 or 5 such that n is less than y; X is a halogen independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, preferably chlorine.
- X may also be a an azide, an isocyanate, a thiocyanate, an isothiocyanate or a cyanide.
- arylalkyl refers to a radical containing both aliphatic and aromatic structures, the radical being at an alkyl position.
- alkylaryl refers to a radical containing both aliphatic and aromatic structures, the radical being at an aryl position.
- Lewis acids include tetraphenylantimony chloride and triphenylantimony dichloride.
- Group 15 Lewis acids useful in this invention may also have the general formula M(RO) n R' m X y - (m+n); wherein M is a Group 15 metal, wherein RO is a monovalent hydrocarboxy radical selected from the group consisting of C1-C30 alkoxy, C7-C30 aryloxy, C7-C30 arylalkoxy, C7-C30 alkylaryloxy radicals; R' is a monovalent hydrocarbon radical selected from the group consisting of C1-C12 alkyl, C6-C10 aryl, C7-C14 arylalkyl and C7-C14 alkylaryl radicals as defined above; n is an integer from 0 to 4 and m is an integer from 0 to 4 and y is 3, 4 or 5 such that the sum of n and m is less than y; X is a halogen independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, preferably chlorine.
- X may also be an azide, an isocyanate, a thiocyanate, an isothiocyanate or a cyanide.
- alkoxy and aryloxy are structural equivalents to alkoxides and phenoxides respectively.
- arylalkoxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an alkoxy position.
- alkylaryl refers to a radical containing both aliphatic and aromatic structures, the radical being at an aryloxy position.
- X may also be an azide, an isocyanate, a thiocyanate, an isothiocyanate or a cyanide.
- arylalkylacyloxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an alkyacyloxy position.
- alkylarylacyloxy refers to a radical containing both aliphatic and aromatic structures, the radical being at an arylacyloxy position.
- Non-limiting examples of these Lewis acids include acetatotetrachloroantimony, (benzoato) tetrachloroantimony, and bismuth acetate chloride.
- Lewis acids such as methylaluminoxane (MAO) and specifically designed weakly coordinating Lewis acids such as B(C 6 F 5 ) 3 are also suitable Lewis acids within the context of the invention.
- Initiators useful in this invention are those initiators which are capable of being complexed with the chosen Lewis acid to yield a complex which reacts with the monomers thereby forming a propagating polymer chain.
- the initiator comprises at least one compound selected from the groups consisting of water, hydrogen halides, carboxylic acids, carboxylic acid halides, sulfonic acids, sulfonic acid halides, alcohols, phenols, tertiary alkyl halides, tertiary aralkyl halides, tertiary alkyl esters, tertiary aralkyl esters, tertiary alkyl ethers, tertiary aralkyl ethers, alkyl halides, aryl halides, alkylaryl halides and arylalkylacid halides.
- Preferred hydrogen halide initiators include hydrogen chloride, hydrogen bromide and hydrogen iodide.
- a particularly preferred hydrogen halide is hydrogen chloride.
- carboxylic acids include both aliphatic and aromatic carboxylic acids.
- carboxylic acids useful in this invention include acetic acid, propanoic acid, butanoic acid; cinnamic acid, benzoic acid, 1 -chloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, p-chlorobenzoic acid, and p-fluorobenzoic acid.
- Particularly preferred carboxylic acids include trichloroacetic acid, trifluoroacteic acid, and p-fluorobenzoic acid.
- Carboxylic acid halides useful in this invention are similar in structure to carboxylic acids with the substitution of a halide for the OH of the acid.
- the halide may be fluoride, chloride, bromide, or iodide, with the chloride being preferred.
- Carboxylic acid halides useful in this invention include acetyl chloride, acetyl bromide, cinnamyl chloride, benzoyl chloride, benzoyl bromide, trichloroacetyl chloride, trifluoroacetylchloride, trifluoroacetyl chloride and p-fluorobenzoylchloride.
- Particularly preferred acid halides include acetyl chloride, acetyl bromide, trichloroacetyl chloride, trifluoroacetyl chloride and p-fluorobenzoyl chloride.
- Sulfonic acids useful as initiators in this invention include both aliphatic and aromatic sulfonic acids.
- preferred sulfonic acids include methanesulfonic acid, trifluoromethanesulfonic acid, trichloromethanesulfonic acid and p-toluenesulfonic acid.
- Sulfonic acid halides useful in this invention are similar in structure to sulfonic acids with the substitution of a halide for the OH of the parent acid.
- the halide may be fluoride, chloride, bromide or iodide, with the chloride being preferred.
- sulfonic acid halides from the parent sulfonic acids are known in the prior art and one skilled in the art should be familiar with these procedures.
- Preferred sulfonic acid halides useful in this invention include methanesulfonyl chloride, methanesulfonyl bromide, trichloromethanesulfonyl chloride, trifluoromethanesulfonyl chloride and p-toluenesulfonyl chloride.
- Alcohols useful in this invention include methanol, ethanol, propanol, 2-propanol, 2- methylpropan-2-ol, cyclohexanol, and benzyl alcohol.
- Phenols useful in this invention include phenol; 2-methylphenol; 2,6-dimethylphenol; p- chlorophenol; p-fluorophenol; 2,3,4,5,6-pentafluorophenol; and 2-hydroxynaphthalene.
- the initiator system may further comprise oxygen- or nitrogen-containing compounds other than the aforementioned to further incluence or enhance the activity.
- Such compounds include ethers, amines, N-heteroaromatic compounds, ketones, sulfones and sulfoxides as well as carboxylic acid esters and amides
- Ethers include methyl ethyl ether, diethyl ether, di-n-propyl ether, tert. -butyl-methyl ether, di-n- butyl ether, tetrahydrofurane, dioxane, anisole or phenetole.
- Amines include n-pentyl amine, ⁇ , ⁇ -diethyl methylamine, ⁇ , ⁇ -dimethyl propylamine, N- methyl butylamine, ⁇ , ⁇ -dimethyl butylamine, N-ethyl butylamine, hexylamine, N-methyl hexylamine, N-butyl propylamine, heptyl amine, 2-amino heptane, 3 -amino heptane, N,N- dipropyl ethyl amine, ⁇ , ⁇ -dimethyl hexylamine, octylamine, aniline, benzylamine, N-methyl aniline, phenethylamine, N-ethyl aniline, 2,6-diethyl aniline, amphetamine, N-propyl aniline, phentermine, N-butyl aniline, ⁇ , ⁇ -diethyl aniline, 2,6-diethy
- N-heteroaromatic compounds include pyridine, 2-,3- or 4-methyl pyridine, dimethyl pyridine, ethylene pyridine and 3-methyl-2-phenyl pyridine.
- Ketones include acetone, butanone, pentanone, hexanone, cyclohexanone, 2,4-hexanedione, acetylacetone and acetonyl acetone.
- Sulfones and sulfoxides include dimethyl sulfoxide, diethyl sulfoxide and sulfolane.
- Carboxylic acid esters include methyl acetate, ethyl acetate, vinyl acetate, propyl acetate, allyl acetate, benzyl acetate, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, dimethyl maleate, diethyl maleate, dipropyl maleate, methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, allyl benzoate, butylidene benzoate, benzyl benzoate, phenylethyl benzoate, dimethyl phthalate, diethyl phthalate, dipropyl phthalate, dibutyl phthalate, dipentyl phthalate, dihexyl phthalate, diheptyl phthalate and dioc
- Carboxylic acid amides include ⁇ , ⁇ -dimethyl formamide, ⁇ , ⁇ -dimethyl acetamide, N,N- diethyl formamide and ⁇ , ⁇ -diethyl acetamide.
- Preferred tertiary alkyl and aralkyl initiators include tertiary compounds represented by the formula below: wherein X is a halogen, pseudohalogen, ether, or ester, or a mixture thereof, preferably a halogen, preferably chloride and Ri, R 2 and R3 are independently any linear, cyclic or branched chain alkyls, aryls or arylalkyls, preferably containing 1 to 15 carbon atoms and more preferably 1 to 8 carbon atoms, n is the number of initiator sites and is a number greater than or equal to 1 , preferably between 1 to 30, more preferably n is a number from 1 to 6.
- arylalkyls may be substituted or unsubstituted.
- arylalkyl is defined to mean a compound containing both aromatic and aliphatic structures.
- Preferred examples of initiators include 2-chloro-2,4,4-trimethylpentane ; 2-bromo-2,4,4-trimethylpentane; 2-chloro-2- methylpropane; 2-bromo-2-methylpropane; 2-chloro-2,4,4,6,6-pentamethylheptane; 2-bromo- 2,4,4,6,6-pentamethylheptane; 1-chloro-l-methylethylbenzene; 1 -chloroadamantane; 1- chloroethylbenzene; 1, 4-bis(l-chloro-l-methylethyl) benzene; 5-tert-butyl- l,3-bis( 1-chloro-l- methylethyl) benzene;
- Another preferred initiator is a polymeric halide, one of Ri, R 2 or R 3 is an olefin polymer and the remaining R groups are defined as above.
- Preferred olefin polymers include polyisobutylene, polypropylene, and polyvinylchloride.
- the polymeric initiator may have halogenated tertiary carbon positioned at the chain end or along or within the backbone of the polymer.
- the olefin polymer has multiple halogen atoms at tertiary carbons, either pendant to or within the polymer backbone, the product may contain polymers which have a comb like structure and/or side chain branching depending on the number and placement of the halogen atoms in the olefin polymer.
- the use of a chain end tertiary polymer halide initiator provides a method for producing a product which may contain block copolymers.
- Particularly preferred initiators may be any of those useful in cationic polymerization of isobutene and butyl rubber include: water, hydrogen chloride, 2-chloro-2,4,4-trimethylpentane, 2-chloro-2-methylpropane, 1 -chloro- 1 -methylethylbenzene, and methanol.
- Initiator systems useful in this invention may further comprise compositions comprising a reactive cation and a weakly-coordinating anion ("WCA") as defined above.
- WCA weakly-coordinating anion
- a preferred mole ratio of Lewis acid to initiator is generally from 1 :5 to 100: 1 preferably from 5: 1 to 100: 1, more preferably from 8: 1 to 20: 1 or, in another embodiment, of from 1 : 1,5 to 15: 1, preferably of from 1 : 1 to 10: 1.
- the initiator system including the lewis acid and the initiator is preferably present in the reaction mixture in an amount of 0.002 to 5.0 wt.-%, preferably of 0.1 to 0.5 wt.-%, based on the weight of the monomers employed.
- the wt. -ratio of monomers employed to lewis acid in particular aluminum trichloride is within a range of 500 to 20000, preferably 1500 to 10000.
- the Lewis acid is ethyl aluminum sesquichloride, preferably generated by mixing equimolar amounts of diethyl aluminum chloride and ethyl aluminum dichloride, preferably in an organic diluent.
- the organic diluent is preferably the same one used to perform the polymerization in step b).
- alkyl aluminum halides are employed water and/or alcohols, preferably water is used as proton source.
- the amount of water is in the range of 0.40 to 4.0 moles of water per mole of aluminum of the alkyl aluminum halides, preferably in the range of 0.5 to 2.5 moles of water per mole of aluminum of the alkyl aluminum halides, most preferably 1 to 2 moles of water per mole of the alkyl aluminum halides.
- aluminum halides in particular aluminum trichloride are employed water and/or alcohols, preferably water is used as proton source.
- the amount of water is in the range of 0.05 to 2.0 moles of water per mole of aluminum in the aluminum halides, preferably in the range of 0.1 to 1.2 moles of water per mole of aluminum in the aluminum halides.
- the organic diluent and the monomers employed are substantially free of water.
- substantially free of water is defined as less than 30 ppm based upon total weight of the reaction medium, preferably less than 20 ppm, more preferably less than 10 ppm, even more preferably less than 5 ppm, and most preferably less than 1 ppm.
- Step b) may be carried out in continuous or batch processes, whereby a continuous operation is preferred.
- the polymerization according to step b) is effected using a polymerization reactor.
- Suitable reactors are those known to the skilled in the art and include flow-through polymerization reactors, plug flow reactor, stirred tank reactors, moving belt or drum reactors, jet or nozzle reactors, tubular reactors, and autorefrigerated boiling-pool reactors. Specific suitable examples are disclosed in WO 2011/000922 A and WO 2012/089823 A.
- the polymerization according to step b) is carried out where the initiator system, the monomer(s), the organic diluent and carbon dioxide form a single phase.
- the polymerization is carried-out in a continuous polymerization process in which the initiator system, the monomer(s), the organic diluent and ethane or carbon dioxide form a single phase.
- the polymerization according to step b) is carried out either as slurry polymerization or solution polymerization.
- the monomers, the initiator system are all typically soluble in the diluent or diluent mixture, i.e., constitute a single phase, while the copolymer upon formation precipitates from the organic diluent. Desirably, reduced or no polymer "swelling" is exhibited as indicated by little or no Tg suppression of the polymer and/or little or no organic diluent mass uptake.
- the monomers, the initiator system are all typically soluble in the diluent or diluent mixture, i.e., constitute a single phase as is the copolymer formed during polymerization.
- Step b) is preferably carried out as solution process.
- step b) is carried out at a temperature in the range of -90 °C to -60°C, preferably in the range of -80 °C to -62 °C and even more preferably in the range of -78 °C to - 65 °C.
- the polymerization temperature is within 20°C above the boiling point of the ethane or the carbon dioxide with the reaction mixture, preferably within 10°C above the boiling point of the ethane or the carbon dioxide.
- the reaction pressure in step b) is typically from 500 to 100,000 hP, preferably from 1100 to 20,000 hPa, more preferably from 1300 to 5,000 hPa.
- the solids content of the slurry in step b) is preferably in the range of from 1 to 45 wt.-%, more preferably 3 to 40 wt.-%, even more preferably 15 to 40 wt.-%.
- solids content or “solids level” refer to weight percent of the polymer in the product medium comprising the polymer, the organic diluent and optionally residual monomer(s) obtained according to step b) but not considering the content of carbon dioxide that might be stll present therein.
- reaction time in step b) is from 2 min to 2 h, preferably from 10 min to 1 h and more preferably from 20 to 45 min.
- the process may be carried out batchwise or continuously. Where a continuous reaction is performed the reaction time given above represents the average residence time.
- the reaction is stopped by quenching agents for example a 1 wt.-% sodium hydroxide solution in water, methanol or ethanol.
- the reaction is quenched by the contact with the aqueous medium in step c), which in one embodiment may have a pH value of 5 to 10, preferably 6 to 9 and more preferably 7 to 9 measured at 20°C and 1013 hPa.
- pH-Adjustment where desired may be performed by addition of acids or alkaline compounds which preferably do not contain multivalent metal ions. pH adjustment to higher pH values is e.g. effected by addition of sodium or potassium hydroxide.
- the conversion is typically stopped after a monomer consumption of from 5 wt.-% to 25 wt.-%, preferably 10 wt.-% to 20 wt.-% of the initially employed monomers.
- Monomer conversion can be tracked by online viscometry or spectroscopic monitoring during the polymerization.
- step c) in particular where step b) was performed as a slurry process, the product medium obtained in step b) is contacted with an aqueous medium and removing at least partially the organic diluent and to the extent present in the medium removing at least partially the residual monomers and carbon dioxide to obtain an aqueous slurry comprising the polyisobutene or the butyl rubber in form of fine particles oftern referred to as rubber crumb.
- the contact can be performed in any vessel suitable for this purpose and be carried out batchwise or contiuously, whereby a continuous process is preferred. In industry such contact is typically performed in a steam-stripper, a flash drum or any other vessel known for separation of a liquid phase and vapours.
- Removal of organic diluent and optionally monomers and/or residual carbon dioxide may also employ other types of distillation so to subsequently or jointly remove the residual monomers and the organic diluent and/or residuakl carbon dioxide to the desired extent. Distillation processes to separate liquids of different boiling points are well known in the art and are described in, for example, the Encyclopedia of Chemical Technology, Kirk Othmer, 4th Edition, pp. 8-31 1, which is incorporated herein by reference. Generally, the unreacted monomers and the diluent may either be seperatly or jointly be recycled into step a) of the process according to the invention.
- the pressure in optional step c) and in one embodiment the steam-stripper or flash drum depends on the organic diluent and monomers employed in step b) and the content of residual carbon dioxide but is typically in the range of from 100 hPa to 5,000 hPa.
- the temperature in optional step c) is selected to be sufficient to at least partially remove the organic diluent and to the extent still present residual monomers and/or carbon dioxide.
- the organic diluent and/or the monomer(s) and/or residual carbon dioxide removed in step c) may be recycled into steps a) and or b) again.
- the temperature is from 10 to 100°C, preferably from 50 to 100°C, more preferably from 60 to 95°C and even more preferably from 75 to 95°C.
- step b) was carried out as solution polymerization upon contact with water the organic diluent is evaporated and the polymer forms discrete particles suspended in the aqueous slurry.
- step d) the polymer contained in the aqueous slurry obtained according to step c) may be separated to obtain the polymer.
- the separation may be effected by flotation, centrifugation, filtration, dewatering in a dewatering extruder or by any other means known to those skilled in the art for the separation of solids from fluids.
- step e) the copolymer particles obtained according to step d) are dried, preferably to a residual content of volatiles of 7,000 or less, preferably 5,000 or less, even more preferably 4,000 or less and in onother embodiment 2,000 ppm or less, preferably 1,000 ppm or less.
- volatiles denotes compounds having a boiling point of below 250°C, preferably 200°C or less at standard pressure and include water as well as remaining organic diluents.
- Drying can be performed using conventional means known to those in the art, which includes drying on a heated mesh conveyor belt or in an extruder.
- a batch polymerization was operated at lab scale with a cooled and agitated reactor having a volume of 1.5 liter intotal.
- the monomers isobutene (99,91%), isoprene and hexane were previously dried with molecular sieve and inhibitor remover for isoprene.
- the monomers (325 g of isobutene, 6.8 g of isoprene), 200 g of hexane and 65 g solid CO 2 were mixed.
- the polymerization was initiated by about 5 g initiator solution.
- the initiator solution was prepared by using ethylaluminumsesquichloride dissolved in technical hexane and activated by traces of water.
- the reaction temperature was -70°C.
- a mixture of Ethanol with 2wt% NaOH was used to stop the polymerization.
- a solution with a polymer content of 18-21 wt% was produced.
- the produced polymer had an average molecular weight of 370 kg/mol and an isoprene content of 1.8 mol% (measured by NMR).
- a batch polymerization was operated at lab scale with a cooled and agitated reactor of 1.5 litre total.
- the monomers isobutene (99,91%), isoprene and hexane were previously dried with molecular sieve and inhibitor remover for isoprene.
- the monomers (325 g of isobutene, 6.8 g of isoprene), 234 g of hexane and 30 g liquid ethane were mixed.
- the polymerization was initiated by about 5 g initiator solution.
- the initiator solution was prepared by using ethylaluminumsesquichloride dissolved in technical hexane and activated by traces of water.
- the reaction temperature was -70°C.
- a mixture of Ethanol with 2wt% NaOH was used to stop the polymerization.
- a solution with a polymer content of 17 wt% was produced.
- the produced polymer had an average molecular weight of 370 kg/mol and an isoprene content of 1.8 mol% (measured by NMR).
- a batch polymerization was operated at lab scale with a cooled and agitated reactor of 1.5 litre total.
- the monomers isobutene (99,91%), isoprene and hexane were previously dried with molecular sieve and inhibitor remover for isoprene.
- the monomers (325 g of isobutene, 6.8 g of isoprene), 200 g of hexane and 65 g liquid ethane were mixed.
- the polymerization was initiated by about 5 g initiator solution.
- the initiator solution was prepared by using ethylaluminumsesquichloride dissolved in technical hexane and activated by traces of water.
- the reaction temperature was -70°C.
- a mixture of Ethanol with 2wt% NaOH was used to stop the polymerization.
- a solution with a polymer content of 17 wt% was produced.
- the produced polymer had an average molecular weight of 270 kg/mol and an isoprene content of 1.8 mol% (measured by NMR).
- a continuous polymerization was operated at pilot scale with two cooled and agitated reactors of 2 litre total capacity each running in a continuous mode.
- the monomers isobutene (99,91%) and isoprene were previously dried in columns filled with molecular sieve and inhibitor remover for isoprene.
- the water content after passing the dry columns was checked off line by Karl- Fischer titration.
- the precooled feeds to the reactors were 3.87 kg/h of isobutene, 0.10 kg/h of isoprene, 1.65 kg/h of technical hexane and 0.38 kg/h liquid ethane .
- the polymerization was initiated by continuous feed of 15 g/h initiator solution.
- the initiator solution was prepared by using ethylaluminumsesquichloride dissolved in technical hexane and activated by traces of water.
- the reaction temperature was -65°C.
- a mixture of Ethanol with 2wt% NaOH was used to stop the polymerization after the reactors.
- a solution with a polymer content of 15 wt% was produced.
- the produced polymer had an average molecular weight of 400- 440 kg/mol and an isoprene content of 1.7-2.0 mol-% (measured by NMR) , the gel-content was range of 0.3wt%.
- the maximum overall run time was 33 h.
- a continuous polymerization was operated at pilot scale with two cooled and agitated reactors of 2 litre total capacity each running in a continuous mode.
- the monomers isobutene (99,91%) and isoprene were previously dried in columns filled with molecular sieve and inhibitor remover for isoprene.
- the water content after passing the dry columns was checked off line by Karl- Fischer titration.
- the precooled feeds to the reactors were 3.87 kg/h of isobutene, 0.10 kg/h of isoprene, 1.40 kg/h of technical hexane and 0.63 kg/h ethane.
- the polymerization was initiated by continuous feed of 12 g/h initiator solution.
- the initiator solution was prepared by using ethylaluminumsesquichloride dissolved in technical hexane and activated by traces of water.
- the reaction temperature was -65°C.
- a mixture of Ethanol with 2 wt% NaOH was used to stop the polymerization after the reactors.
- a solution with a polymer content of 12 wt% was produced.
- the produced polymer had an average molecular weight of 430 kg/mol and an isoprene content of 1.7-1.9 mol-% (measured by NMR) , the gel-content was range of 0.3 wt%.
- the overall run time was 16 h.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP17181176 | 2017-07-13 | ||
PCT/EP2018/068392 WO2019011814A1 (en) | 2017-07-13 | 2018-07-06 | PROCESS FOR THE PRODUCTION OF ISOBUTENE POLYMERS WITH ENHANCED TEMPERATURE CONTROL |
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EP3652224A1 true EP3652224A1 (en) | 2020-05-20 |
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ID=59387884
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EP18738295.7A Withdrawn EP3652224A1 (en) | 2017-07-13 | 2018-07-06 | Process for the production of isobutene polymers with improved temperature control |
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US (1) | US20210147590A1 (ru) |
EP (1) | EP3652224A1 (ru) |
JP (1) | JP2020526639A (ru) |
KR (1) | KR20200030561A (ru) |
CN (1) | CN111094367A (ru) |
CA (1) | CA3069643A1 (ru) |
RU (1) | RU2764774C2 (ru) |
SG (1) | SG11202000231QA (ru) |
WO (1) | WO2019011814A1 (ru) |
Family Cites Families (25)
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GB543308A (en) | 1938-12-31 | 1942-02-19 | Standard Oil Dev Co | An improved manufacture of polymerisation products |
US2545144A (en) * | 1943-04-21 | 1951-03-13 | Standard Oil Dev Co | Process and apparatus for the production of high molecular weight polymers |
US2468523A (en) * | 1943-06-10 | 1949-04-26 | Standard Oil Dev Co | Delayed-action polymerization process |
GB589393A (en) * | 1944-11-14 | 1947-06-19 | Standard Oil Dev Co | Improved process for the low temperature polymerization of olefinic materials |
DE2936361A1 (de) | 1979-09-08 | 1981-04-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von polyisobutylenen |
DE3010870A1 (de) | 1980-03-21 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur polymerisation von isobutylen |
US4400493A (en) | 1982-04-07 | 1983-08-23 | Cosden Technology, Inc. | Polymerization of isobutylene |
DE3404764A1 (de) | 1984-02-10 | 1985-08-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur polymerisation von isobutylen |
DE3509272A1 (de) | 1985-03-15 | 1986-09-18 | Basf Ag, 6700 Ludwigshafen | Katalysatorsystem fuer die kationische polymerisation von isobutylen |
DE3527551A1 (de) | 1985-08-01 | 1987-02-05 | Basf Ag | Verfahren zur polymerisation von isobutylen |
US4946899A (en) | 1988-12-16 | 1990-08-07 | The University Of Akron | Thermoplastic elastomers of isobutylene and process of preparation |
DE4428024A1 (de) * | 1994-08-08 | 1996-02-15 | Bayer Ag | Verfahren zur Herstellung von Polyisoolefinen |
US5763544A (en) | 1997-01-16 | 1998-06-09 | Praxair Technology, Inc. | Cryogenic cooling of exothermic reactor |
DE19948947A1 (de) * | 1999-10-11 | 2001-04-12 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Polyisobutenen |
CN1332986C (zh) * | 2002-12-20 | 2007-08-22 | 埃克森美孚化学专利公司 | 聚合方法 |
CA2510860C (en) * | 2002-12-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Polymerization process utilizing hydrofluorocarbons as diluents |
US7582715B2 (en) | 2002-12-20 | 2009-09-01 | Exxonmobil Chemical Patents Inc. | Polymers substantially free of long chain branching |
US20080290049A1 (en) * | 2004-06-23 | 2008-11-27 | Timothy Daniel Shaffer | Methods for Separating Slurry Components |
US7893176B2 (en) * | 2007-03-23 | 2011-02-22 | Exxonmobil Chemical Patents Inc. | Polydispersity-controlled isoolefin polymerization with polymorphogenates |
EP2303935B1 (en) | 2008-07-15 | 2015-01-14 | LANXESS International SA | Common solvent process for producing high molecular weight halobutyl rubber |
WO2010099201A1 (en) * | 2009-02-24 | 2010-09-02 | Gevo, Inc. | Methods of preparing renewable butadiene and renewable isoprene |
EP2269727A1 (de) | 2009-07-01 | 2011-01-05 | LANXESS International SA | Rohrreaktor und Verfahren zur kontinuierlichen Polymerisation |
RU2586976C2 (ru) | 2010-01-20 | 2016-06-10 | Ланксесс Интернасьональ Са | Способ получения высокомолекулярного галогенированного каучука с использованием общего растворителя |
EP2471594A1 (de) | 2010-12-29 | 2012-07-04 | LANXESS International SA | Reaktor und Verfahren zur kontinuierlichen Polymerisation |
EP3137512B1 (en) * | 2014-04-30 | 2021-05-26 | Arlanxeo Singapore Pte. Ltd. | Diluent for the production of butyl rubber |
-
2018
- 2018-07-06 SG SG11202000231QA patent/SG11202000231QA/en unknown
- 2018-07-06 KR KR1020207004090A patent/KR20200030561A/ko not_active Application Discontinuation
- 2018-07-06 EP EP18738295.7A patent/EP3652224A1/en not_active Withdrawn
- 2018-07-06 CN CN201880059384.0A patent/CN111094367A/zh active Pending
- 2018-07-06 JP JP2020501215A patent/JP2020526639A/ja active Pending
- 2018-07-06 WO PCT/EP2018/068392 patent/WO2019011814A1/en unknown
- 2018-07-06 CA CA3069643A patent/CA3069643A1/en active Pending
- 2018-07-06 US US16/629,634 patent/US20210147590A1/en not_active Abandoned
- 2018-07-06 RU RU2020106315A patent/RU2764774C2/ru active
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RU2764774C2 (ru) | 2022-01-21 |
WO2019011814A1 (en) | 2019-01-17 |
JP2020526639A (ja) | 2020-08-31 |
US20210147590A1 (en) | 2021-05-20 |
KR20200030561A (ko) | 2020-03-20 |
CN111094367A (zh) | 2020-05-01 |
RU2020106315A (ru) | 2021-08-13 |
RU2020106315A3 (ru) | 2021-08-13 |
SG11202000231QA (en) | 2020-02-27 |
CA3069643A1 (en) | 2019-01-17 |
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